【药物名称】MF-10058
化学结构式(Chemical Structure):
参考文献No.46826
标题:Selective M2 muscarinic receptor antagonists having 5H-dibenz[b,f]azepine structure
作者:Imbimbo, B.P.; Mandelli, G.R.; Terni, P.M.L.; Maiorana, S. (Mediolanum Farmaceutici)
来源:WO 0102386
合成路线图解说明:

Horner-Emmons reaction of 1-benzyl-4-piperidone (I) with triethyl 4-phosphonocrotonate (II) afforded the (piperidinylidene)butenoate (III). Catalytic hydrogenation of the double bond of (III) with concomitant N-debenzylation yielded the piperidinylbutanoate (IV). After reprotection as the N-benzyl derivative (V), reduction of the ester function of (V) using LiAlH4 gave alcohol (VI), which was further converted to mesylate (VII). Displacement of the mesylate group of (VII) with diethylamine produced diamine (VIII). The N-benzyl group of (VIII) was then deprotected by transfer hydrogenation to furnish piperidine (IX). The chloroacetyl derivative (XI) was prepared by acylation of iminodibenzyl (X) with chloroacetyl chloride. Chloride (XI) was finally condensed with piperidine (IX) in the presence of Na2CO3 and NaI to afford the title compound.

参考文献No.597240
标题:Synthesis of new cardioselective M2 muscarinic receptor antagonists
作者:Mandelli, G.R.; Maiorana, S.; Terni, P.; Lamperti, G.; Colibretti, M.L.; Imbimbo, B.P.
来源:Chem Pharm Bull 2000,48(11),1611
合成路线图解说明:

Horner-Emmons reaction of 1-benzyl-4-piperidone (I) with triethyl 4-phosphonocrotonate (II) afforded the (piperidinylidene)butenoate (III). Catalytic hydrogenation of the double bond of (III) with concomitant N-debenzylation yielded the piperidinylbutanoate (IV). After reprotection as the N-benzyl derivative (V), reduction of the ester function of (V) using LiAlH4 gave alcohol (VI), which was further converted to mesylate (VII). Displacement of the mesylate group of (VII) with diethylamine produced diamine (VIII). The N-benzyl group of (VIII) was then deprotected by transfer hydrogenation to furnish piperidine (IX). The chloroacetyl derivative (XI) was prepared by acylation of iminodibenzyl (X) with chloroacetyl chloride. Chloride (XI) was finally condensed with piperidine (IX) in the presence of Na2CO3 and NaI to afford the title compound.

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